WO2004056926A1 - Colorants azoiques phtalimidyle, procedes de preparation et d'utilisation de ces derniers - Google Patents

Colorants azoiques phtalimidyle, procedes de preparation et d'utilisation de ces derniers Download PDF

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Publication number
WO2004056926A1
WO2004056926A1 PCT/EP2003/050956 EP0350956W WO2004056926A1 WO 2004056926 A1 WO2004056926 A1 WO 2004056926A1 EP 0350956 W EP0350956 W EP 0350956W WO 2004056926 A1 WO2004056926 A1 WO 2004056926A1
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WO
WIPO (PCT)
Prior art keywords
formula
dye
dyes
synthetic
materials
Prior art date
Application number
PCT/EP2003/050956
Other languages
English (en)
Inventor
Antoine Clément
Alfons Arquint
Urs Lauk
Original Assignee
Ciba Specialty Chemicals Holding Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ciba Specialty Chemicals Holding Inc. filed Critical Ciba Specialty Chemicals Holding Inc.
Priority to EP20030799542 priority Critical patent/EP1572808A1/fr
Priority to JP2004561487A priority patent/JP2006510772A/ja
Priority to US10/538,892 priority patent/US7169909B2/en
Priority to AU2003300262A priority patent/AU2003300262A1/en
Publication of WO2004056926A1 publication Critical patent/WO2004056926A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
    • C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
    • C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
    • C09B29/3634—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O) from diazotized heterocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
    • C09B29/0033—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom containing a five-membered heterocyclic ring with one nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/922—Polyester fiber
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/30—Woven fabric [i.e., woven strand or strip material]

Definitions

  • Phthalimidyl azo dves processes for the preparation thereof and the use thereof
  • the present invention relates to disperse dyes having an N-al yl-phthalimide diazo component and a pyridone coupling component, to processes for the preparation of such dyes and to the use thereof in dyeing or printing semi-synthetic and especially synthetic hydrophobic fibre materials, more especially textile materials.
  • Disperse azo dyes having an N-alkyl-phthalimide diazo component and a pyridone coupling component have been known for a long time and are used in dyeing hydrophobic fibre materials. It has, however, been found that the dyeings or prints obtained using the currently known dyes do not in ail cases satisfy today's requirements, especially in respect of fastness to washing and fastness to perspiration. There is therefore a need for new dyes that especially have good washing fastness properties.
  • the present invention accordingly relates to disperse dyes that yield dyeings having a high degree of fastness to washing and to perspiration and that, in addition, have good build-up characteristics both in the exhaust and thermosol processes and in textile printing.
  • the dyes are also suitable for discharge printing.
  • the dyes according to the invention correspond to formula
  • R-i is CrC ⁇ 2 alkyl or -C n H 2 n-(OCH 2 CH 2 )m-OR 3 , n being a number from 2 to 8, m being a number from 0 to 4 and R 3 being d-C ⁇ alkyl, C 6 -C 24 aryl or C 6 -C 2 aralkyl, R 2 is methyl, ethyl, n-propyl, n-butyl, 2-methoxyethyl or 2-ethoxyethyl, X is halogen and Y is hydrogen, chlorine or bromine.
  • CrC 12 Alkyl as Ri and R 3 may be, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, neopentyl, n-hexyl, n-octyl, n-decyl or n-dodecyl.
  • C 6 -C 24 Aryl groups as R 3 are, for example, phenyl, tolyl, mesityl, isityl, naphthyl and anthryl.
  • Suitable C ⁇ -C 24 aralkyl groups are, for example, benzyl and 2-phenylethyl.
  • R 2 is preferably n-butyl.
  • Halogen as X is fluorine, chlorine or, preferably, bromine.
  • Y is preferably hydrogen.
  • the present invention relates also to the process for the preparation of the dyes of formula (1), which comprises nitration of a phthalimide of formula
  • R 2 is as defined hereinbefore, in the acid range, as described, for example, on page 459 in Organic Synthesis, Collective Volume 2, (a Revised Edition of Annual Volumes X-XIX), J.Wiley & Sons, followed by alkylation of the resulting nitro compound, for example in accordance with a method described in Journal of Organic Chemistry 32 (1967) on page 1923, paragraph 3, and, for example after a reductive treatment described in Bull. Soc. Chim. de France 1957 on page 569, conversion into an intermediate of formula
  • the halogenation is carried out, for example, by reacting the compound of formula (3) first with sodium acetate in acetic acid and then with bromine in the same medium to form the corresponding monobromo compound.
  • the diazotisation is likewise carried out in a manner known perse, for example with sodium nitrite in an acidic, for example hydrochloric-acid-containing or sulfuric-acid-containing, aqueous medium.
  • the diazotisation may, however, also be carried out using other diazotisation agents, e.g. using nitrosylsulfuric acid.
  • an additional acid may be present in the reaction medium, e.g. phosphoric acid, sulfuric acid, acetic acid, propionic acid, hydrochloric acid or mixtures of such acids, e.g. mixtures of propionic acid and acetic acid.
  • the diazotisation is advantageously carried out at temperatures of from -10 to 30°C, e.g. from -10°C to room temperature.
  • the coupling of the diazotised compound to the coupling component of formula (4) is likewise effected in known manner, for example in an acidic, aqueous or aqueous-organic medium, advantageously at temperatures of from -10 to 30°C, especially below 10°C.
  • acids used are hydrochloric acid, acetic acid, propionic acid, sulfuric acid and phosphoric acid.
  • diazo components and the coupling components of formula (4) are known or can be prepared in a manner known perse.
  • the present invention relates also to dye mixtures comprising at least two structurally different azo dyes of formula (1).
  • the dye mixtures according to the invention comprising at least two structurally different azo dyes of formula (1) can be prepared, for example, by simply mixing the individual dyes.
  • the amounts of the individual dyes in the dye mixtures according to the invention can vary within a wide range, for example from 95:5 to 5:95 parts by weight, especially from 70:30 to 30:70 parts by weight, more especially from 55:45 to 45:55 parts by weight, of the individual dyes in a dye mixture comprising two azo dyes according to the invention.
  • the dyes and dye mixtures according to the invention may be used for dyeing or printing semi-synthetic and especially synthetic hydrophobic fibre materials, more especially textile materials.
  • Textile materials composed of blend fabrics that comprise such semi-synthetic or synthetic hydrophobic fibre materials can also be dyed or printed using the dyes or dye mixtures according to the invention.
  • Semi-synthetic fibre materials that come into consideration are, especially, cellulose 2 1 / 2 - acetate and cellulose triacetate.
  • Synthetic hydrophobic fibre materials consist especially of linear, aromatic polyesters, for example those of terephthalic acid and glycols, especially ethylene glycol, or condensation products of terephthalic acid and 1,4-bis(hydroxymethyl)cyclohexane; of polycarbonates, e.g. those of ⁇ , ⁇ -dimethyl-4,4-dihydroxy-diphenylmethane and phosgene, and of fibres based on polyvinyl chloride or on polyamide.
  • polyester fibre materials are dyed in the exhaust process from an aqueous dispersion in the presence of customary anionic or non-ionic dispersants and, optionally, customary swelling agents (carriers) at temperatures of from 80 to 140°C.
  • Cellulose 2 1 / 2 -acetate is dyed preferably at from 65 to 85°C and cellulose triacetate at temperatures of from 65 to 115°C.
  • the dyes and dye mixtures according to the invention will not colour wool and cotton present at the same time in the dyebath or will colour such materials only slightly (very good reservation) so that they can also be used satisfactorily in the dyeing of polyester/wool and polyester/cellulosic fibre blend fabrics.
  • the dyes and dye mixtures according to the invention are suitable for dyeing in accordance with the thermosol process, in the exhaust process and for printing processes.
  • the said fibre materials can be in a variety of processing forms, e.g. in the form of fibres, yarns or nonwoven, woven or knitted fabrics.
  • the dye is ground so that its particle size is on average from 0.1 to 10 microns. Grinding can be carried out in the presence of dispersants. For example, the dried dye is ground together with a dispersant or kneaded into a paste form together with a dispersant and then dried in vacuo or by atomisation. After adding water, the resulting preparations can be used to prepare printing pastes and dyebaths.
  • the customary thickeners will be used, e.g. modified or unmodified natural products, for example alginates, British gum, gum arabic, crystal gum, locust bean flour, tragacanth, carboxymethyl cellulose, hydroxyethyl cellulose, starch or synthetic products, for example polyacrylamides, polyacrylic acid or copolymers thereof, or polyvinyl alcohols.
  • the dyes and dye mixtures according to the invention impart to the said materials, especially to polyester materials, level colour shades having very good in-use fastness properties such as, especially, good fastness to light, fastness to heat setting, fastness to pleating, fastness to chlorine, and wet fastness, e.g. fastness to water, to perspiration and to washing; the finished dyeings are further characterised by very good fastness to rubbing. Special emphasis should be given to the good fastness properties of the dyeings obtained with respect to perspiration and, especially, to washing.
  • the dyes and dye mixtures according to the invention can also be used satisfactorily in producing mixed shades together with other dyes.
  • the dyes and dye mixtures according to the invention are also well suited to dyeing hydrophobic fibre materials from supercritical C0 2 .
  • the present invention relates to the above-mentioned use of the dyes and dye mixtures according to the invention as well as to a process for the dyeing or printing of semi-synthetic or synthetic hydrophobic fibre materials, especially textile materials, in which process a dye according to the invention is applied to the said materials or incorporated into them.
  • the said hydrophobic fibre materials are preferably textile polyester materials. Further substrates that can be treated by the process according to the invention and preferred process conditions can be found hereinbefore in the more detailed description of the use of the dyes according to the invention.
  • the invention relates also to hydrophobic fibre materials, preferably polyester textile materials, dyed or printed by the said process.
  • the dyes according to the invention are, in addition, suitable for modern reproduction processes, e.g. thermotransfer printing.
  • Example 1.1 Analogously to Example 1.1 , the following dyes can be prepared, which are likewise suitable for dyeing semi-synthetic or synthetic hydrophobic fibre materials (Table 1):
  • a 1 % dyeing (based on the dye and the substrate) is produced on woven polyester fabric by the high-temperature exhaust process at 130°C and is cleared reductively.
  • the violet dyeing obtained in that manner has very good in-use fastness properties, especially excellent fastness to washing.
  • thermosol process 10 g/litre of dye, liquor pick-up 50 %, fixing temperature 210°C.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Coloring (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne des colorants représentés par la formule (I) dans laquelle R1 représente alkyle C1-C12 ou -CnH2n-(OCH2CH2)m-OR3, n étant un nombre compris entre 2 et 8, m étant un nombre compris entre 0 et 4 et R3 représentant alkyle C1-C12, aryle C6-C24 ou aralkyle C6-C24, R2 représente méthyle, éthyle, n-propyle, n-butyle, 2-méthoxyéthyle ou 2-éthoxyéthyle, X représente halogène et Y représente hydrogène, chlore ou brome. Cette invention se rapporte également au procédé de préparation de ces colorants et à leur utilisation pour colorer ou imprimer des matériaux en fibres semi-synthétiques et plus particulièrement en fibres hydrophobes synthétiques, plus spécifiquement des matériaux textiles. Formule (I)
PCT/EP2003/050956 2002-12-19 2003-12-08 Colorants azoiques phtalimidyle, procedes de preparation et d'utilisation de ces derniers WO2004056926A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP20030799542 EP1572808A1 (fr) 2002-12-19 2003-12-08 Colorants phtalimidylazoiques jaunes a base de 3-cyano-4-methyl-6 hydroxy-2-pyridones et de 4-amino-n-alkylphtalimides halogenees
JP2004561487A JP2006510772A (ja) 2002-12-19 2003-12-08 フタルイミジルアゾ染料、その製造方法、およびその使用
US10/538,892 US7169909B2 (en) 2002-12-19 2003-12-08 Phthalimidylazo dyes, processess for the preparation thereof and the use thereof
AU2003300262A AU2003300262A1 (en) 2002-12-19 2003-12-08 Phthalimidylazo dyes, processes for the preparation thereof and the use thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP02406118.6 2002-12-19
EP02406118 2002-12-19

Publications (1)

Publication Number Publication Date
WO2004056926A1 true WO2004056926A1 (fr) 2004-07-08

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PCT/EP2003/050956 WO2004056926A1 (fr) 2002-12-19 2003-12-08 Colorants azoiques phtalimidyle, procedes de preparation et d'utilisation de ces derniers

Country Status (8)

Country Link
US (1) US7169909B2 (fr)
EP (1) EP1572808A1 (fr)
JP (1) JP2006510772A (fr)
KR (1) KR20050085747A (fr)
CN (1) CN1729253A (fr)
AU (1) AU2003300262A1 (fr)
TW (1) TW200422353A (fr)
WO (1) WO2004056926A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103965094A (zh) * 2013-01-31 2014-08-06 江苏道博化工有限公司 N-甲基-4-氨基-5-溴-邻苯二甲酰亚胺的合成方法
WO2017202480A1 (fr) * 2016-05-25 2017-11-30 Huntsman Advanced Materials (Switzerland) Gmbh Colorants azoïques dispersés, leur procédé de préparation et d'utilisation

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* Cited by examiner, † Cited by third party
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DE102006054088A1 (de) * 2006-11-16 2008-05-21 Siemens Ag Messvorrichtung und Messverfahren zum Inspizieren einer Oberfläche eines Substrates
US8696766B2 (en) * 2008-03-25 2014-04-15 Dystar Colours Deutschland Gmbh Azopyridone disperse dyes, their preparation and use
CN104479395A (zh) * 2014-11-18 2015-04-01 杭州福莱蒽特精细化工有限公司 一种高水洗牢度和高日晒牢度的分散染料及其制备方法
CN114437564B (zh) * 2022-02-28 2024-04-02 浙江万丰化工股份有限公司 一种高牢度分散染料组合物及其应用
CN116396625A (zh) * 2022-06-30 2023-07-07 浙江龙盛集团股份有限公司 一种分散橙染料组合物及其制品

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1302221A (fr) * 1969-04-03 1973-01-04
JPS5285584A (en) * 1976-01-12 1977-07-15 Mitsubishi Chem Ind Dyeing method of synthetic fibers
JPS53119930A (en) * 1977-03-29 1978-10-19 Mitsubishi Chem Ind Ltd Production of pyridone azo dye
JPS53138431A (en) * 1977-05-10 1978-12-02 Mitsubishi Chem Ind Ltd Production of pyridone type azo dyes
JPS53138432A (en) * 1977-05-10 1978-12-02 Mitsubishi Chem Ind Ltd Production of pyridone type azo dyes

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3923776A (en) 1969-04-03 1975-12-02 Basf Ag Monoazo dye from an aminobenzene carboxylic ester diazo component and a pyridone coupling component
US4133806A (en) 1969-04-03 1979-01-09 Basf Aktiengesellschaft Azo dyes with an N-substituted 2-hydroxy-3-cyano-4-methyl pyrridone-6-coupling component
JPS5378381A (en) * 1976-12-22 1978-07-11 Mitsubishi Chem Ind Dyeing of syntetic fibers
JP3265063B2 (ja) * 1993-07-12 2002-03-11 三井化学株式会社 感熱転写記録用色素、感熱転写記録用インキ組成物及び転写シート
TWI243192B (en) * 1998-12-31 2005-11-11 Ciba Sc Holding Ag Phthalimidyl azo pigments, method for producing same and utilization thereof
RU2283328C2 (ru) * 2001-02-07 2006-09-10 Циба Спешиалти Кемикэлз Холдинг Инк. Фталимидилазокрасители и их применение
US7087731B2 (en) * 2001-02-07 2006-08-08 Ciba Specialty Chemicals Corporation Phthalimidyl azo dyes, process for the preparation thereof and the use thereof
ATE544822T1 (de) * 2002-03-22 2012-02-15 Huntsman Adv Mat Switzerland Azofarbstoffe

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1302221A (fr) * 1969-04-03 1973-01-04
JPS5285584A (en) * 1976-01-12 1977-07-15 Mitsubishi Chem Ind Dyeing method of synthetic fibers
JPS53119930A (en) * 1977-03-29 1978-10-19 Mitsubishi Chem Ind Ltd Production of pyridone azo dye
JPS53138431A (en) * 1977-05-10 1978-12-02 Mitsubishi Chem Ind Ltd Production of pyridone type azo dyes
JPS53138432A (en) * 1977-05-10 1978-12-02 Mitsubishi Chem Ind Ltd Production of pyridone type azo dyes

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 197735, Derwent World Patents Index; Class A60, AN 1977-61950Y, XP002260144 *
DATABASE WPI Section Ch Week 197847, Derwent World Patents Index; Class A60, AN 1978-84875A, XP002260146 *
DATABASE WPI Section Ch Week 197903, Derwent World Patents Index; Class A60, AN 1979-04691B, XP002260145 *
DATABASE WPI Section Ch Week 197903, Derwent World Patents Index; Class A60, AN 1979-04692B, XP002260147 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103965094A (zh) * 2013-01-31 2014-08-06 江苏道博化工有限公司 N-甲基-4-氨基-5-溴-邻苯二甲酰亚胺的合成方法
WO2017202480A1 (fr) * 2016-05-25 2017-11-30 Huntsman Advanced Materials (Switzerland) Gmbh Colorants azoïques dispersés, leur procédé de préparation et d'utilisation
US10934435B2 (en) 2016-05-25 2021-03-02 Huntsman International Llc Disperse azo dyes, a process for the preparation thereof and the use thereof

Also Published As

Publication number Publication date
US7169909B2 (en) 2007-01-30
AU2003300262A1 (en) 2004-07-14
KR20050085747A (ko) 2005-08-29
US20060046596A1 (en) 2006-03-02
CN1729253A (zh) 2006-02-01
JP2006510772A (ja) 2006-03-30
TW200422353A (en) 2004-11-01
EP1572808A1 (fr) 2005-09-14

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